Rare Hunter S. Thompson Collectibles Featured In Covetable Christie’s Auction

Memorabilia from the “Fear and Loathing in Las Vegas” legend is up for grabs in the Jim Irsay Collection.

Christie’s auction house is offering three rare Hunter S. Thompson-owned collectibles amid a massive trove of totemic pieces spanning musical instruments, movies, literature, and sports. 

The legendary Fear and Loathing in Las Vegas author and hard-living “gonzo” journalist had an inimitable personal style that included Hawaiian shirts, aviator shades, plastic sun visors, and old-timey cigarette holders, a look that was memorably channeled by Johnny Depp in Terry Gilliam’s 1998 movie adaptation of Fear and Loathing. Thompson was also a devoted fan of white canvas Converse All-Stars. A pair worn by the writer that’s mounted in a shadowbox is now being offered through the Jim Irsay Collection auction with an estimated value of $1,000 to $1,500. 

But the biggest ticket Thompson item is a cherry-red 1973 Chevrolet Caprice Classic with a white leather interior and white soft top known as “The Red Shark.” Owned by the gonzo guru from 1990 until his death in 2005, the head-turning beauty was driven by Depp and Benicio del Toro in the film. The historic Chevy comes with an black box filled with assorted Thompson road trip ephemera, including “Jacques Marie Mage Los Angeles Aviator Sunglasses, two Jimmy Buffett cassette tapes, one Allman Brothers cassette tape, various documents concerning Holley Carburetor Model 4011, and [a] user manual for Sony EXR-10/14 FM/AM Cassette Car Stereo.” 

Rounding out the Thompson-affiliated trio is his weathered copy of Jack Kerouac’s Beat Generation classic Dharma Bums. The first edition book features multiple ink and pencil annotations. On page 170, Thompson circled the word “Now”, and noted: “use of ‘now’ in past tense—very effective, immediate” and elsewhere marveled at the length of Kerouac’s sentences and mused about “hornrimmed intellectual hepcats with wild black hair.” The book could sell for $2,000 to $3,000. (The Irsay collection also features Kerouac’s original typescript scroll of On The Road, the definitive Beat novel, that’s estimated to go for anywhere from $2.5 million-$4 million.)

“The items in Irsay’s collection are tangible links to Hunter S. Thompson and his signature style of Gonzo journalism,” Heather Weintraub, Christie’s specialist in books and manuscripts, said in a statement to Maxim. “Thompson’s irreverent way of writing dissolved the boundary between observer and participant—instead of reporting from the outside, he became a character on the inside. As part of his wild story, he relinquished any objectivity. Little captures his brand of anarchy and defiance more than the legendary Caprice, aka the ‘Red Shark,’ Thompson’s personal car that was used in the film adaptation of his most famous work, 1972’s Fear and Loathing in Las Vegas. In the book, his anti-hero (and partially fictionalized alter-ego) Raoul Duke drove a fictionalized version of the car.”

Fascinating as these finds may be for Thompson fans, the infamous former Rolling Stone scribe is merely a footnote in the sprawling Christie’s collection. Irsay, the late memorabilia-obsessed owner and CEO of the Indianapolis Colts, was perhaps best known for his epic cache of historic guitars, which Guitar World magazine has called “The Greatest Guitar Collection on Earth.” 

Among the offerings at a “Hall of Fame” live sale beginning March 12 is the 1966 Fender Mustang guitar that Kurt Cobain played on Nirvana’s Nevermind and In Utero recording sessions and in the “Smells Like Teen Spirit” music video. The hallowed instrument is expected to fetch anywhere from $2.5 million-$5 million.

David Gilmour’s “Black Strat” is also for sale. He played the famed all-black Fender Stratocaster on Pink Floyd’s The Dark Side of the Moon (1973), Wish You Were Here (1975), Animals (1977) andThe Wall (1979). Notably, you can hear it in “Money,” “Shine On You Crazy Diamond,” and the “Comfortably Numb” solo, arguably Gilmour’s most famous. It’s estimated to sell for $2 million-$4 million. The third-most valuable guitar on offer is Jerry Garcia’s custom-made “Tiger” that the Grateful Dead frontman played onstage from 1979-89, including at his final Dead performance at Chicago’s Soldier Field on July 9, 1995. It’s estimated to hammer for $1 million-$2 million.

Outside literature and rock, the Irsay collection includes landmark sports items like Wayne Gretzky’s 1986-87 Edmonton Oilers jersey, worn when he scored his 500th NHL goal and during game 7 of the 1987 Stanley Cup finals; Secretariat’s saddle from the famed racehorse’s Triple Crown win in 1973; and Sylvester Stallone’s handwritten script notebook for the Oscar-winning boxing classic Rocky. The Jim Irsay Collection is set to feature four auctions through March 17 and a New York public exhibition from March 6 to 12.